Whether congenital or acquired, basic principles must be followed in the management of web space contractures. Nonoperative methods are often effective in preventing or limiting the degree of web contractures if initiated early after the traumatic event. Nonoperative methods include early splinting and passive and active range of motion exercises. If operative intervention is required for established contractures or for conditions where contractures are likely to form, the options that allow for durable coverage and minimal postoperative contracture formation are the most desirable. Many variations and combinations of Z-plasties, V-Y, and V-M advancements have been described. The surgeon should follow principles of reconstruction and be versed in several options to optimize the outcome. The first web space has the added challenge of the need for thumb motion in multiple planes. Local rotation-advancement flaps are useful for minor skin contractures, but greater degrees of adduction require larger amounts of high-quality tissue, such as that of a regional flap or free tissue transfer. These procedures should be done in the acute phase in trauma situations where it is obvious that tissue loss leads to first web contracture.